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1346549-11-8

4-chloro-6-[(1,1-diMethylethyl)sulfonyl]quinoline synthesis

6synthesis methods
6-(tert-butylthio)-4-chloroquinoline

1346549-09-4
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4-chloro-6-[(1,1-diMethylethyl)sulfonyl]quinoline

1346549-11-8
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Yield:1346549-11-8 80%

Reaction Conditions:

with Oxone in methanol;water at 20;

Steps:

2.2

4-Chloro-6-[(1,1-dimethylethyl)thio]quinoline (9.4 g, 37 mmol) was suspended in MeOH (100 mL) and water (100 mL) before oxone (25 g, 41 mmol) was added and the reaction was stirred at rt until complete by LCMS (3 hours). The MeOH was removed in vacuo and the heterogeneous aqueous solution was extracted 3* with 100 mL EtOAc. The combined organics were concentrated to provide 8.5 g (80%) of a yellow powder. 1H NMR (DMSO-d6) δ: 9.08 (d, J=4.8 Hz, 1H), 8.63 (d, J=2.0 Hz, 1H), 8.36 (d, J=8.8 Hz, 1H), 8.20 (dd, J=8.8, 2.0 Hz, 1H), 8.00 (d, J=4.8 Hz, 1H), 1.32 (s, 9H); MS (m/z) 284.1 (M+H+).

References:

US2012/41024,2012,A1 Location in patent:Page/Page column 16-17